
Holiday rentals in Sheboygan County
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Top-rated holiday rentals in Sheboygan County
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Other great holiday rentals in Sheboygan County

Home in Plymouth
4.92 out of 5 average rating, 13 reviewsthe getaway at crystal lake!
MikeRating, 5 stars45 months ago
This is a warm, inviting home with a terrific location in the lake. Jana and Josh’s house was very comfortable, clean, spacious and stocked with everything we needed for our vacation. An absolutely beautiful spot on the lake. Jana and Josh were extremely helpful and generous hosts who really anticipate what guests may need. We loved our stay!
Superhost

Cottage in Random Lake
4.84 out of 5 average rating, 67 reviewsPrivate 3 bedroom lake house
HoaRating, 5 stars3 weeks ago
Awesome place. We will be back!

Apartment in Sheboygan
5 out of 5 average rating, 8 reviews'Beautiful Day Getaway' - Lake Michigan Views
KathrynRating, 5 stars9 months ago
We loved our stay and can’t wait to be back. The house was perfect for our party of 8 and had tons of room for everyone as well as good communal space.
Guest favourite

Flat in Sheboygan
4.85 out of 5 average rating, 61 reviewsFully Loaded and Clean! King
StevenRating, 5 stars2 months ago
Great stay in Sheboygan! So close to the harbor and downtown it was great! Highly recommend the Italian restaurant trattoria and the other 2 places associated w them. Our stay was a great place to hang out and relax as well as a base of operations for local adventures!
Guest favourite

Cottage in Random Lake
5 out of 5 average rating, 8 reviewsCozy Lakefront Escape: Ideal Seasonal Getaway
CheyanneRating, 5 stars3 months ago
Such a beautiful and peaceful place. Host is very friendly and responsive. First time I’ve woken up feeling well rested in a minute, beds really helped any of our back issues. Main parking spots might not be available at first due to people parking there for ice fishing on the lake but plenty of street parking. If staying in the winter, run the water for a moment to run through any sediment in the pipes. (Not a house problem, just winter in Wisconsin.) :)
Superhost

Home in Sheboygan
4.77 out of 5 average rating, 13 reviews3 Bedroom Beach House
KatieRating, 5 stars21 months ago
Place was great! Only comment I have is the beds were too soft (I need a firmer bed) :)
Top guest favourite

Home in Oostburg
5 out of 5 average rating, 11 reviewsSurfDaze! A Lake Michigan property
JosephRating, 5 stars1 month ago
We had an incredible stay at SurfDaze! The pictures don’t do it justice—this is a truly stunning beachfront property on Lake Michigan. The home was spotless, beautifully maintained, and exceptionally comfortable. Waking up to the sound of the waves and enjoying the breathtaking views made our trip unforgettable. We can’t wait to come back!
Top guest favourite

Home in Sheboygan
4.95 out of 5 average rating, 43 reviewsWander Back Inn to Sheboygan
JaimieRating, 5 stars2 days ago
Karlee was quick to respond to some concerns that we had while staying there. The concern wasn’t anything major but was still responsive. The place was as described and more. The place was spacious and plenty of rooms for everyone. Love that her place was close to the highway and Walmart! Highly recommend this place.
Destinations to explore
- Rentals with a hot tub Sheboygan County
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- Family-friendly rentals Sheboygan County
- Rentals with a washing machine and dryer Sheboygan County
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- Milwaukee Public Museum
- Erin Hills Golf Course
- Kohler-Andrae State Park
- Whistling Straits Golf Course
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Heiliger Huegel Ski Club
- Bradford Beach
- Harrington Beach State Park
- Pine Hills Country Club
- Trout Springs Winery
- Sunburst
- Discovery World
- West Bend Country Club
- Blue Mound Golf and Country Club